Hexylamine → 2-(4-{4-[5-(4-tert-Butylphenyl)-4-methyl-4H-[1,2,4]-triazol-3-ylsulfanyl]-2-heptyloxybenzyl amino}phenyl)-N-hexylacetamide

HRID 1171445Notes

Reaction equation

HRID 1171445 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]([CH3:43])[C:13]([S:16][C:17]3[CH:34]=[CH:33][C:20]([CH2:21][NH:22][C:23]4[CH:28]=[CH:27][C:26]([CH2:29][C:30]([OH:32])=O)=[CH:25][CH:24]=4)=[C:19]([O:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[CH:18]=3)=[N:14][N:15]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[N:44]1(O)[C:48]2[CH:49]=[CH:50][CH:51]=[CH:52][C:47]=2N=N1.C(N)CCCCC.CN(C)CCCN=C=NCC>CN(C)C=O.O>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]([CH3:43])[C:13]([S:16][C:17]3[CH:34]=[CH:33][C:20]([CH2:21][NH:22][C:23]4[CH:24]=[CH:25][C:26]([CH2:29][C:30]([NH:44][CH2:48][CH2:47][CH2:52][CH2:51][CH2:50][CH3:49])=[O:32])=[CH:27][CH:28]=4)=[C:19]([O:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[CH:18]=3)=[N:14][N:15]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 8102HexylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 11157700(4-{4-[5-(4-tert-Butylphenyl)-4-methyl-4H-[1,2,4}-triazol-3-ylsulfanyl]-2-heptyloxybenzylamino}phenyl)acetic acid

Product 1

HCID 111582142-(4-{4-[5-(4-tert-Butylphenyl)-4-methyl-4H-[1,2,4]-triazol-3-ylsulfanyl]-2-heptyloxybenzyl amino}phenyl)-N-hexylacetamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of (4-{4-[5-(4-tert-butylphenyl)-4-methyl-4H-[1,2,4]-triazol-3-ylsulfanyl]-2-heptyloxybenzyl amino}phenyl)acetic acid (0.3 g, 0.5 mmol), benzotriazol-1-ol (0.074 g, 0.55 mmol) in dimethylformamide (10 ml) is stirred for 20 minutes. n-Hexylamine (0.066 ml, 0.5 mmol) and (3-dimethylaminopropyl)ethylcarbodiimide (0.105 g, 0.55 mmol) are added and then the medium is stirred for 24 hours at room temperature. The addition of water causes the formation of a precipitate which is dried before being purified by chromatography on a silica column, eluted with a heptane/ethyl acetate (3/7) mixture. After evaporation of the solvents, 0.205 g (60%) of the expected compound is recovered.

Workup

  1. customis dried
  2. custombefore being purified by chromatography on a silica column
  3. washeluted with a heptane/ethyl acetate (3/7) mixture
  4. customAfter evaporation of the solvents, 0.205 g (60%) of the expected compound
  5. customis recovered

Sources & evidence

ORD record
ord-9bbac46f9c4f4bd786dc261dcd6e2cb0
Source dataset
uspto-grants-2010_11
Patent number
US07829588B2

Reaction notes

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